


bad bet

by auberjonois



Category: The Simpsons
Genre: Anal Sex, Blow Jobs, M/M, Office Sex, Plot What Plot/Porn Without Plot, Semi-Public Sex, a can of Coke and a competitive streak can be used as an excuse for anything, even less plot than the last one......
Language: English
Status: Completed
Published: 2020-05-29
Updated: 2020-05-29
Packaged: 2021-03-03 01:14:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,734
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24446422
Author URL: https://archiveofourown.org/users/auberjonois/pseuds/auberjonois
Summary: Monty is willing to win a bet at any cost, but Smithers isn’t likely to make it easy for him.
Relationships: Charles Montgomery Burns/Waylon Smithers
Comments: 7
Kudos: 54





	bad bet

**Author's Note:**

> can’t go a minute without being horny or hating corporate scum

Monty Burns wasn’t a man who turned down a challenge, but as he drums his fingers on the top of his desk waiting for the company executives to arrive he is seriously reconsidering his decision to take this bet. Smithers bumps against his foot again and grunts, Burns looks down at his assistant beneath the desk, watching him as he folds his legs underneath his body. Smithers peers back up at him and smiles with a sort of deviousness that Burns saw only on occasion. It startles him sometimes, just what sort of plots his normally even-tempered companion could cook up in that head of his.

Smithers leans forward a bit, his arms on either side of Burns’ legs on the chair. He rests his chin on Burns’ lap looking contented and not at all concerned by what was about to unfold. 

And why should he be? Burns thinks to himself unless they were found out Smithers would escape embarrassment while he himself might not come out of this meeting unscathed. 

“Are you alright?” 

“Hm?”

“Are you alright?” Smithers’ voice is soft and he places a firm hand on Burns’ thigh, the sly glint in his eyes had vanished for now. “We don’t have to do this.”

“A bet is a bet,” Burns replies and he plucks Smithers’ glasses from his nose.

“You can call it off,” Smithers continues, Burns wonders if he was beginning to have his own doubts about their little escapade, “No loss.”

Monty peers into the thick lenses of Smithers’ glasses, staring at the warped lines of his office walls through the frames. Smithers is damn near blind without them, but he hardly needed to see well for this particular task. 

“You know that’s not true.” 

Smithers most likely knows that he won’t take the out, but, considerate until the end, he’d offered it. Burns feels a pang of affection, Smithers was much too soft on him in a way Monty had never known but appreciated nonetheless. 

He folds the arms of Smithers’ glasses and slips them neatly into his breast pocket while Waylon, now gone quiet, draws his fingers along Burns’ inner thigh in a way that in any other context would make him moan. But for now, he would have to stifle it, there is a sharp rap of knuckles on his office door announcing the arrival of his executives. 

“Come in,” 

The response to his voice is immediate, the heavy wood door swings open and each of the Burns Corp. executives file in with measured steps. As they cross the expansive office there’s a tug at his belt, then at the button of his trousers, then his zipper is being undone, the sound it makes is horrifyingly loud to Monty who is sure the gig is up. 

But the executives don’t seem to register it, their stride doesn’t falter and they each take a seat in one of the chairs facing Burns’ desk, all except the CFO who goes about setting up an entirely pointless poster board on an easel, a large graph of their Q3 earnings. As if Burns isn’t privy to this information already. 

He hates all his executives, but it’s possible he hates the CFO, with his beady eyes and greasy Enron charm, the most.

Oh.

He’s momentarily distracted from mentally eviscerating these desk jockeys when Waylon’s fingers run up the front of his boxers, along the sensitive underside of his cock. Any other day and Monty might have been embarrassed by just how fast he’d gotten hard, Waylon had hardly even begun to touch him, but he was hyper-aware of every light touch he’d received so far with an audience in front of him, the stakes are high and it doesn’t help that Smithers’ soft hands know every one of his weaknesses. 

“Good morning, Mr. Burns,” the COO announces with a convivial pep in her voice. Outside of formalities, she was all piss and vinegar which Burns could appreciate, but she usually put on a slick, affable demeanor that he could see through a mile away. 

“Good morning, now that those pleasantries are over, get on with this report, we haven’t got all day to dedicate to stroking you lot’s egos.” Burns snarls this and in response, he feels the palm of Waylon’s hand slide against his dick, no fabric separating their skin now. He clenches his fist on the desk.

“Um,” the nasal voice of the Burns Corp. VP pipes up, he is glancing around the office nervously. “Shouldn’t we wait for Mr. Smithers?”

“He’s preoccupied at the moment,” Monty replies, and how right he was. Burns could feel the scrape of that sentence on the back of his throat, brought on by the soft but deliberate tongue that is currently making its way from the base of Monty’s cock to its tip for the second time. 

If anyone else heard the shake in his voice they don’t mention it, instead sharing a brief glance amongst each other as if all concerned about Smithers’ uncharacteristic absence. 

“Well?” Burns demands, pressing on even as Waylon takes the head of his cock between his lips and teases it gently with his tongue. He could already feel his thigh begin to twitch, Waylon was far too good at this for Monty to even stand a chance at winning the bet. 

As the CFO launches into his dry presentation, Monty is already clenching and unclenching his fist on the desk, trying his damndest not to reach beneath it to hold onto the back of Waylon’s head as he continued to work his tongue in circles over Monty’s dick. He grits his teeth and hopes that whatever tense expression he has on his face at the moment is registered only as contempt by his executives.

He’d hoped concentrating on earning speculations for the next quarter would be enough to distract him from Waylon’s mouth but Burns realizes now he’d made a severe miscalculation.

He’d bet Smithers a Coke that he couldn’t make Monty cum during this meeting. And, like Burns himself, Waylon had a competitive streak, he was no stranger to playing dirty tricks to get his way. 

He was proving that fact at this very moment, Monty stares blearily at the graph his CFO is pointing at as he drones on, Waylon is slowly taking every inch of Burns’ cock into this throat all while stroking the sensitive skin of Monty’s inner thigh with one hand and pinning his hips down firmly with the other. Waylon’s pace is excruciating, Monty wants nothing more than to buck up into his tight throat and teach him a lesson about being such a tease.

Maybe he could get away with reaching a hand beneath his desk and pushing Waylon’s head down, tugging at his graying hair in the process, it would be risky. But the executives would surely notice if he gave in to his urge to simply fuck Waylon’s mouth until he finally came down his assistant’s throat. It would be embarrassing, although he has to admit, thrilling as well, to expose himself as such a flagrant voyeur. Even more pressing, however, is the matter of losing the bet. 

So in lieu of either of those actions, Burns chooses to instead lace his fingers together and set his hands neatly on the desk in front of him, tuning back into the presentation. He can feel eyes on him, the COO is staring at him, a plucked eyebrow just barely raised. Burns glares back even as his cock slides down Smithers’ throat for the third time. Waylon swallows and the brief but extraordinary tightness makes Monty flinch.

Damn.

“Are you alright, sir?” It’s the COO, she can tell something is amiss, if only she could imagine what was occurring right under their noses.

“I’m fine,” Burns replies in a low voice, the hoarseness is even harder to hide now. He swallows, “Well? Why have you stopped? Go on! I haven’t got time for inane questions!” 

Smithers has pulled off Monty’s dick as he waits to see if another executive will speak up, though he is still tracing delicate patterns on Monty’s hip and his hot breath on Monty’s oversensitive cock is almost too much to bear. 

“You look flushed, sir,” the CFO chimes in, his graph forgotten for the moment. 

Monty can feel the heat that began on the bridge of his nose before spreading out across his cheeks intensify, half need, half fury. Smithers had once called the CFO the Chief Fuck Off and Monty wants nothing more than to tell the executive just that. 

Well, maybe there’s one thing he wants more. 

“Don’t make me repeat myself,” he grinds out finally. 

If the CFO or any of the other spineless bunch have something to say they keep it to themselves and the presentation continues. 

Waylon resumes teasing Monty’s cock in an instant, lapping up the pre-cum that had gathered there in the minute or so he wasn’t slavishly sucking Monty’s dick. 

Despite the interruption the coil in Burns’ gut is tightening, Smithers draws him into his warm mouth once again his soft tongue and lips are gliding over Monty’s twitching cock.

He knows he won’t make it unless he plays just as dirty as Smithers. 

Slumping down only slightly in his chair, Burns slides his left foot over Waylon’s thigh before making contact with the swell of his erection, pinned beneath the fabric of his trousers. 

Waylon tenses when he does, his grip tightening on Monty’s hip. Monty applies pressure.

The reaction is instantaneous. Waylon’s whole body jerks as if he’s been scalded and he pulls off Burns’ dick. As he does, he lets a breathy moan escape his mouth. It’s short and low but the executives have heard it. Again the room is quiet as they all process what they’ve just heard.

Burns smiles at them and coughs politely into his hand, breaking the silence. The CFO is clearly bewildered, he clears his throat and gathers himself enough to continue on. In fact now nearly all the executives have turned their gaze back to the poster board as if suddenly enraptured by the speculative earnings. Only the VP’s wide eyes linger on Burns for a few seconds more before he too turns away and focuses on the CFO’s hand gesturing around the graph. 

Monty glances down for just a moment and nearly groans himself. Waylon’s chin is resting on his thigh, his eyes half-shut, and his lips parted as Monty continues to apply a firm pressure on his cock. It hadn’t taken much and already Smithers looked close to the edge. Monty wishes he could reach down and stroke Waylon’s hair in that soothing motion that he knows would make Waylon swoon against his leg.

Burns looks back up at the graph, shifting his foot slightly as he does, taking some of its pressure off of Smithers. Waylon squirms against him, seeking out any friction, and leans further into Burns’ lap as he grinds against the hard sole of Monty’s shoe. 

Monty smiles to himself, what he wouldn’t give to make Waylon cum right now with just the frictionless pressure of his shoe. He teases Waylon with soft and quick presses as if he were tapping his foot on the floor and feels the tips of Waylon’s fingers bite into the flesh of his hip. There’s no doubt Smithers is trying desperately to hold back another soft moan, he must know the executives heard the last one. 

It’s just his luck that the CFO, looking pale and flustered, seems to be wrapping up his presentation. He glances nervously at the other executives.

“Uh, any questions?”

There’s silence from the gathered executives who usually take this time to extoll the virtues of their own work and participate in shallow back-patting. 

The CFO swallows and faces Burns. “Er, Mr. Burns?” 

Burns quirks a brow at him as he rolls his foot over Waylon’s hard-on yet again, feeling his assistant twitch against his lap. 

“See yourselves out,” he mutters and flicks his wrist towards the door. 

The executives waste no time, leaping out of their chairs, and bustling out of the office, the door slams behind them. As soon as it does Monty pushes away from his desk.

He stands and looks down at Waylon, still on his knees, and dazed from the sudden loss of contact. 

“Get up, you,” Burns demands, there’s hardly any edge to his voice though and when Waylon begins to haul himself up from beneath the desk Monty finds himself leaning forward to help Smithers up. 

Waylon is in his arms in an instant lurching towards Burns with a woozy smile on his lips. His expression is watery and he’s staring up at Monty with soft needy eyes.

Monty kisses him hard on the lips and Waylon sinks into it so easily, his mouth is warm and wet and the kiss is sloppy until Burns catches Waylon’s lower lip with his teeth and bites down hard. 

Smithers’ shocked yelp is loud enough to be a scream and Monty wonders if the executives have made it far enough down the hall so as not to hear it. Though it seems fairly certain that they’d caught onto their boss’ little game. Or they had put the clues together to at least make an educated guess about what exactly was keeping Smithers preoccupied.

Burns trails his hands down Waylon’s chest, taking a moment to palm him through the front of his pants. Waylon reacts immediately, his grip on Monty’s arms tightens and he kisses back deeper and more frantically as Monty teases him. Burns reaches for Smithers’ belt and pulls it apart before undoing his fly and slipping a hand into his boxers. Waylon’s cock is throbbing and wet with pre-cum as he ruts shamelessly into Monty’s fist. 

Monty breaks the kiss, Waylon’s eyes look less hazy with want, he’s sobered up from whatever trance he’d been in if only just barely. Burns lets go of Waylon’s dick and raises his hands to shove lightly at his chest. 

“On the desk,” he orders. 

“Yes, sir,” Smithers groans, his voice is thick with need. Monty feels his cock throb as he watches Waylon shove his pants and boxers down from his hips before turning his back to Burns and bending over the desk just as he was ordered to do. 

Monty takes his cock in his hand and rolls his palm over the head as he runs his palm over the smooth pale skin of Waylon’s ass. Waylon is trembling slightly as he does, it’s most likely taking all his self-control not to shake his ass and simply beg for Monty to fuck him hard. 

That will come in due time, Burns thinks, for now, he wants to savor this moment. He lifts his hand from Smithers’ warm skin and reaches down to open a drawer in his desk. He takes the bottle of lube from it and pops the lid open with his thumbnail.

He squeezes a bit out and slicks his left middle finger before dropping the bottle onto the desk and spreading Waylon’s ass with his right hand giving him a satisfying view of Waylon’s tight hole.

He can feel Smithers’ eyes on him, he’s peering over his shoulder from where his head is resting on the desk, pleading for Monty to touch him. He doesn’t have to wait long, Burns draws his slick finger over Waylon’s asshole and he gasps loudly, his whole body twitching on the hard top of the desk. 

Monty smiles to himself as he slips his finger in and feels the muscles tighten around it as Waylon’s breathing becomes heavier and the flush on his cheeks continues to intensify. 

Smithers had already prepped himself before this whole game had started, the sweetheart, so pressing his finger against Waylon’s prostate and teasing him like this is simply for Monty’s own pleasure as he watches Waylon quiver on top of the desk, muttering pleas for more under his breath. Burns is at his limit as well and he draws his finger from Waylon quickly, savoring the shocked hiss that escapes Waylon’s mouth. Smithers’ self-control wavers and he rolls his hips back, searching for something more satisfying to fill him. 

Monty swallows hard at the sight of his assistant begging to be fucked. He grabs for the bottle of lube again, squeezing out more into his fingers and smearing it onto his dick. 

“Such a slut,” he hisses and steps forward, his left hand on his cock, with his right he spreads Waylon open again. 

“Yes, sir,” Smithers replies, his vocabulary reduced to monosyllables as Monty teases his hole with the tip of his dick. 

Burns can hardly contain himself any longer and he shoves into Waylon, fingers digging into Waylon’s skin when the head of his cock pushes through the tight ring of muscles, and a jolt races up his body as he sinks into the heat. 

He’s so close to the edge already, the memory of nearly coming down Waylon’s throat in front of the executives is still fresh and Monty takes a moment to steel himself and savor the feeling of Waylon twitching around his cock. 

He spends this time teasing Smithers, Monty leans down and wraps his fingers around Waylon’s erection, pumping it slowly and listening to the sounds that Waylon is making low in his throat. 

Monty draws patterns with his nails on the sensitive skin of Waylon’s exposed lower back, where his rumpled shirt has been shoved up haphazardly, feeling his swollen cock twitch beneath his hand as he lightly strokes it with just the tips of his fingers. Drops of pre-cum are leaking from the head of Waylon’s cock and running down the hot skin, Monty dips his fingers into it and gathers some. 

He leans forward, drawing his hand away from Waylon’s erection, Waylon moans as Monty’s cock sinks deeper into him, and lifts his fingers smeared with pre-cum up to Waylon’s lips. Smithers wastes no time, he laps at Monty’s fingers hungrily.

“Look at how wet you are for me,” Burns murmurs, doling out praise he knows Smithers will swoon for, “That’s it, such a good boy.” 

Smithers can only whimper in response as Monty rolls his hips and pulls his hand away, reaching down again to wrap his fingers around Waylon’s dick as he begins to fuck into him.

Waylon pushes his hips back into every thrust, he’s whining so loudly now, already unable to form coherent thoughts as he’s railed against the desk. Monty rests his chin on Waylon’s shoulder, wrapping an arm around him and pulling him close. 

“Should’ve had you right there in front of them,” he growls, “next time I’ll fuck you like this while they prattle on.”

Waylon hisses out something that sounds like an affirmative. Monty groans, sinking his teeth into Waylon’s shoulder, hard enough for him to feel through the thin fabric of his shirt, and imagining the executives again in their seats watching as Smithers is fucked senseless across the desk. He squeezes Waylon’s dick firmly as he strokes it faster. He knows Waylon is close from the desperate sounds he’s making and the way he’s fucking himself on Burns’ dick. 

Monty lets up on Waylon’s shoulder and moves quickly to a sensitive spot on his neck, just above his shirt collar, where he nips him again and sucks on the tender skin. It’s all too much for Waylon finally, Monty can feel his cock pulsing in his hand and cum spills over his fingers, spattering onto the desk.

Waylon is shuddering but still rolls his hips back as he rides out his orgasm, determined that Monty not be far behind him. And he’s not, the thought of using Waylon in front of the Burns Corp. executives, proving to them just how loyal he is to Monty, making him cum in front of them, it’s all too much and finally, Burns empties himself into Waylon with a low growl, appreciating how Waylon still thrusts back slowly on his cock, milking each wave of his orgasm from him. 

They lie there for a moment panting before Monty gathers himself enough to pull out of Waylon’s ass, close the front of his trousers, and slump back into his chair. 

Smithers takes his time, though it's more for show, Burns watches mesmerized as his cum leaks out of Waylon and runs down his thigh. Monty can’t help himself, he leans forward in his chair and drags his tongue up Waylon’s leg, following the wet trail up to Waylon’s well-fucked ass where he teases his over-sensitive hole. 

Waylon squirms on the desk and keens as Monty laps at the tender skin, dipping his tongue in occasionally just to hear Waylon gasp. 

“Monty, please,” Smithers finally chokes out, clearly unable to handle anymore teasing.

Burns lets out a self-satisfied hum and finally relents, easing himself back into his chair and taking the time to wipe away the mess on his hands with a handkerchief as Waylon dresses. When he finishes neatly tucking in his shirt, Waylon bends down to kiss Monty softly on the mouth.

He pulls away after a moment.

“You won,” he admits, though Monty can hardly say Waylon looks broken up about his loss. “I owe you a Coke.”

Monty smirks at him and pulls Smithers’ glasses from his breast pocket, handing them over. Waylon looks grateful as he slides them on and adjusts them on his nose. 

“Well, what are you dawdling for?” Monty replies, crossing his legs haughtily. 

Waylon’s face reddens again, “Now? Sir, the executives...”

“Heard you make that undignified noise, yes, I was there, you’ll have to face them soon enough.” Monty smirks back at him, “Might as well tear the bandage off.” 

Waylon doesn’t look convinced but sighs in defeat and checks his wallet for a couple of dollar bills. 

Satisfied that he’s at least got the money so that he isn’t caught unawares by one of the executives lurking around the vending machine, Waylon kisses Monty’s cheek and hurries off, hoping that he can dodge being seen until the whole incident is mostly forgotten. 

Burns is left alone in his office half-dozing while appraising the smears of cum Waylon left on his desk. Maybe, Monty thinks, when Smithers returns with the can of Coke he’ll have him clean up that mess.

**Author's Note:**

> another 4am fic which had to be edited fairly extensively since part of it was written drunk... but i hope y’all enjoyed ; ;


End file.
